Pricing Should Feel Like a Scam to Both People

I was on a coaching call recently with a guy running a program for professional speakers. He's booking 110 calls a month through LinkedIn and cold email, charging $6,800 for his core offer, doing about $40-50K a month in revenue. By most agency standards, that's a business that's working. And he knew it. He didn't come to me because things were falling apart - he came because he was thinking about his backend offer, specifically a monthly management retainer for clients who graduated the program.

He'd thought about a price point. He told me he was considering $1,299 a month.

I asked him why.

He said something like, "I just want to be fair to the client."

That word - fair - is where most pricing goes wrong. Because fair is not the goal. Fair is a price that leaves money on the table while simultaneously making you feel underpaid. Fair is the zone where no one wins.

Here's what I actually told him about pricing, and it's something I've said a hundred times but never gets old: the price should feel like a scam to both people.

The client should look at the deal and privately think, I can't believe they're charging this little. I'm getting away with something here.

And you should look at the deal and privately think, I can't believe they're paying this much for what I'm actually doing. I'm getting away with something here.

That productive tension - both sides feeling like they have the better end of it - that's the sweet spot. That's a deal that holds. That's a client relationship that sticks. That's what pricing is supposed to feel like when it's set correctly.

Why Most Founders Anchor on the Wrong Thing

When most people set prices, they do it backwards. They start with their own cost - the hours, the team, the tools, the overhead - and then they add a margin on top. That's a cost-plus model, and it's fine if you're manufacturing widgets. It's terrible if you're selling outcomes.

This guy's retainer would involve a cold email strategist managing campaign launches, maintaining lead flow, and making sure the speaker's outbound machine keeps running. He was thinking about paying that strategist roughly $199 per client per month. Add in some tool costs, and he's probably at $300-400 in hard cost per client. So he looks at that and thinks, "Well, $1,299 seems reasonable. I'm making almost $900 margin per client."

Sounds logical. Completely wrong.

The problem is that $1,299 is priced against his costs. It has nothing to do with what the client is actually buying.

What's the client buying? They're buying a fully managed outbound system that books them paid speaking gigs. And what does one paid speaking gig generate for one of his clients? We were talking about speakers charging between $5,000 and $25,000 per gig. One booking - one - could generate 4x to 20x the cost of the monthly retainer. The math on that is so obviously in the client's favor that $1,299 a month is almost laughably cheap if you're delivering even one gig per month.

Once you stop pricing against your cost and start pricing against the client's outcome, the number gets bigger. And when you actually believe in what you're selling - when you've seen it work, when you have case studies, when a client just closed a $17,000 deal in Hawaii and has more meetings booked - the number should get a lot bigger.

The Other Failure: the Fake Price Test

There's a version of this problem on the front-end too. He mentioned he was thinking about testing $6,800 versus $7,500 as price points for his main program.

I stopped him right there. That's not a pricing test. That's rounding up by $700. If somebody can't pay $6,800, they almost certainly can't pay $7,500 either. And if they can pay $7,500, they probably could've paid $9,800. The buyer who can afford $6,800 and the buyer who can afford $12,000 are often the exact same person. The difference is how you present the offer, how much confidence you project, and whether the social proof backs up the number.

A real pricing test is $6,800 versus $12,000. Not $6,800 versus $7,500.

Most people are terrified to run that test because they've already convinced themselves the higher number won't work. But they don't know. They've never tried it. And in my experience, when you've built a program that's actually delivering results - when clients are booking gigs, closing deals, and running outbound systems that work - you are almost always undercharging. Not by $700. By thousands.

Pricing Psychology Is Weird, and You Should Use That

While we were talking, I also mentioned something about the $1,299 price point that he'd landed on. The issue isn't just that it's too low - it's that the number itself has no authority. It's a number that looks like someone did a quick calculation and stopped there.

Here's a thing I've noticed: $1,999 sometimes feels like more money than $2,500. That sounds insane, but it's true. The $1,999 is in "almost two thousand" territory. The $2,500 reads as a round, clean, confident number - and somehow that makes it feel more accessible, not less. More importantly, $2,500 is a thousand dollars more per client per month. If you have 20 clients on that retainer, that's $20,000 a month you left on the table by going with $1,299 instead.

Play with the numbers. Not because you're trying to trick anyone, but because pricing signals something about how you see your own offer. A weird, small number says "I wasn't sure what to charge." A clean, confident number says "this is what it costs."

The Version of This That Actually Gets Interesting

Here's where the conversation went next, and where I think the real opportunity is for anyone selling a service where outcomes are quantifiable.

We were talking about some of his clients who were killing it - speakers who are booking gigs, closing deals, building real momentum. One guy closed a $17K gig in Hawaii with more meetings already lined up. He's the kind of client who, if his outbound machine stays running, could generate $30,000 to $40,000 a month in speaking revenue. Maybe more.

For a client like that, a flat $2,500 monthly retainer is fine. But there's a more interesting structure available: a base retainer plus a commission on bookings.

The framing I suggested: your base rate is $2,500 a month. That's the floor - it covers the management, the campaigns, the lead flow. But we're also going to take 30% of every gig we close for you. And the minimum is always $2,500, even in a slow month. But if we book you a $20K gig? Now you're paying $6,000 that month instead. And you're still making $14K you wouldn't have had without us.

That's a deal where the client thinks they're getting away with something - because they are. They're paying nothing up front, they're keeping 70% of every booking, and they have a team running their outbound for them. And you think you're getting away with something - because you've built a machine that can book gigs at scale, and you're taking a cut of the upside without the risk of performing on stage.

Both sides feel like they scammed the other. That's the goal.

What This Looks Like Applied to the Cold Email Pitch

We also spent time workshopping the actual cold email strategy for one of his speakers - a former CMO who ran the marketing team for Pepsi and led the Google Play launch, now doing speaking and consulting on resilience for fast-growing teams.

The email angle I put together in real time: "I ran the marketing team for Pepsi and Google and now I help burnt-out teams navigate change in fast-growing environments. I'd love to discuss a workshop at [company] to help catch any issues before they happen. I've done similar work for Walmart, Meta, Scotiabank, and more. Let's hop on a quick call."

That's it. Direct ask. No "are you the right person?" dance. No multi-step inquisitive sequence. Just: here's who I am, here's the problem I solve, here's who I've done it for, let's talk.

The education market this company serves - K-12 schools, colleges - responds well to the inquisitive approach because the decision chain is simpler. Corporate is different. CEOs and department heads are getting pitched constantly. They respect directness. Go for the ask.

And on the targeting: for this kind of speaker, with name-brand case studies like Walmart and Meta in the deck, I told him to go broad. Pull the biggest companies by employee count - 30,000 to 50,000 contacts - and email the CEO. You're not expecting the CEO of a Fortune 500 company to personally book a speaker. But you are expecting him to forward the email to whoever handles it internally. And when a CEO forwards something, it gets handled. That's the play.

You can scrape a list like that fast. Tools like ScraperCity's B2B database, Apollo, or similar platforms let you filter by company size and pull contact data at scale. The targeting on this one is simple - largest companies by headcount, active CEO, send.

If you want the actual email frameworks we use for outreach like this, I've put together my top 5 cold email scripts - grab those and you'll have a solid starting point to adapt for your own clients or offers.

A Note on Deliverability (Because It Matters More Than Copy)

He mentioned he's currently setting clients up with 10 domains, 20 mailboxes, on Google Workspace. I told him to watch our cold email infrastructure training, because we've moved completely off Google and Outlook.

The reason is simple: Google and Outlook can see all your inboxes and associate them together. When one gets flagged, they all suffer. We moved to custom infrastructure - our own mail servers hosted on Microsoft Azure, completely separate from the major providers. Deliverability has been clean ever since we made the switch.

The specific thing to watch for: some inbox providers market themselves as "custom infrastructure" but are actually just white-labeling Google Workspace accounts behind the scenes. If the provider's selling point is Gmail and Outlook delivery, run. You want to see actual custom SMTP with their own servers. Mail Reef and Hypertide are examples of providers doing it right. If you're not sure who your provider is using under the hood, ask them directly. The answer will tell you everything.

He also mentioned he's switching from Smartlead to Instantly and is impressed by the AI reply agent - it saves a significant amount of time managing responses at scale, and from what I've seen it performs well for high-volume campaigns. Worth testing if you're not already using it.

The Bigger Picture: Stop Thinking Like a Service Business

At one point in the call, he said something that I hear from a lot of smart operators: "I'm more of a systems guy. My brain goes to infrastructure - what team do we need, how do we fulfill this?"

That instinct is good. You need to be able to fulfill. But if you let it run unchecked, you end up building a machine to service a price point that's too low, instead of finding the right price point first and then building the machine to support it.

The correct order is: figure out the price that feels like a scam to both sides. Then build the infrastructure to deliver it at that price. Not the other way around.

Think about what his business could look like at the premium tier. He mentioned that Charlie Rocket - Grammy-winning music mogul, Nike "Dream Crazy" campaign, keynote speaker commanding $40,000 a gig - had actually reached out to him about the outbound system. That's a speaker who's already proven. Bureaus represent him. He's got the credibility.

If you can take a speaker like that and become their dedicated booking operation - running targeted outbound, handling the pitch, negotiating the fee, closing the gig - you don't need 50 clients paying $1,299 a month. You need five clients paying you 20% of their bookings. One $50,000 gig generates $10,000. Book that speaker four times in a month and you've made $40,000 from one relationship.

That's not a cold email agency. That's a talent agency. And talent agencies don't race to the bottom on pricing. They represent who they believe in, they go find the biggest rooms possible, and they take their cut of the outcome.

The traditional speakers bureau model only works for about 1% of speakers - the ones who are already famous enough to book themselves. Everybody else is sitting on six bureaus that aren't doing anything for them. That's the opening. That's where outbound changes the game entirely, and that's where pricing based on outcomes - not cost - becomes the obvious move.

The Exercise I'd Run If You're Stuck on Price Right Now

Here's what I'd do if you're not sure whether your price is right:

• Find your best case study. Not your average client. Your best one. The one who closed the biggest deal, got the best result, made the most money because of your service.
• Calculate their ROI from working with you. Not a vague estimate. An actual number. If your service cost $2,500 a month and they made $30,000 because of it, that's a 12x return in one month.
• Ask yourself: at what price does the ROI still feel insane to the client? If it's 12x at $2,500, it's still 6x at $5,000. Is 6x still a no-brainer? Probably yes. Keep going.
• Ask yourself: at what price does your margin start feeling thin? If your all-in cost per client is $400, you have a ton of room. If your cost is $2,200, you don't.
• The number where both answers overlap - where the client's ROI is still obvious and your margin is strong - that's your starting price. Not your ceiling.

And then test it. Don't test $6,800 versus $7,500. Test $6,800 versus $12,000. Run 30 sales conversations at each price point and see what happens. You'll learn more from that test than from six months of theoretical pricing research.

If you want a full breakdown of how to structure your outreach, your offers, and your backend to support higher-ticket pricing, the 7-Figure Agency Blueprint covers all of it - grab it for free.

The goal isn't a price that feels fair. Fair is the comfort zone that keeps you small. The goal is a price where your client can't believe how good the deal is, and you can't believe how much they're paying for something you could do in your sleep. Find that number. Test it. Then raise it again.